Hydrochloric Acid → HCID 178427600, compound

HRID 322549Notes

Reaction equation

HRID 322549 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.[NH:11]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@H:12]([C:30](N(OC)C)=[O:31])[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[NH:29])[NH:18][S:19]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20].[Li]C1SC=CN=1.Cl.C1C[O:53]CC1>>[NH:11]([C:36]([O:38][C:39]([CH3:42])([CH3:40])[CH3:41])=[O:37])[C@H:12]([C:30]([OH:53])=[O:31])[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[NH:29])[NH:18][S:19]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:20])=[O:21].[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 9256ThiazoleHCID 178418339ButyllithiumHCID 178502742HCID 178502742, compoundHCID 178506781HCID 178506781, compound

Product 1

HCID 178427600HCID 178427600, compoundYield 84%

Procedure

To a solution of thiazole (2.5 g, 29 mmol) in THF (25 mL) at −78° C. was added n-BuLi (1.6 M in hexane, 19 mL) dropwise. The mixture was stirred for 30 min. Then a solution of Boc—Arg(Tos)—N(Me)OMe (1.7 g, 3.6 mmol) in THF(50 mL) was added to the lithiothiazole mixture at −78° C. The solution was stirred for 2 h. 1 M HCl (30 mL) was added to the reaction mixture and warmed to room temperature. The mixture was extracted with EtOAc (100 mL). The organic layer was washed with sat. NaCl (30 mL), dried over MgSO4, filtered and evaporated. The crude oily residue was purified by flash column over silica gel(50% EtOAc in CH2Cl2) to give Boc—Arg(Tos)—Thiazole (1.5 g, 84% yield) as a white powder. DCl—MS(M+H)+=496

Workup

  1. stirringThe solution was stirred for 2 h
  2. extractionThe mixture was extracted with EtOAc (100 mL)
  3. washThe organic layer was washed with sat. NaCl (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude oily residue was purified by flash column over silica gel(50% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-8be0502e08ea4fc9a2cd0a35ef9c7306
Source dataset
uspto-grants-2001_04
Patent number
US06211154B1

Reaction notes

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